(2R,5S)-1-aza-6-benzhydryl-7-ethoxycarbonyl-3-oxa-8-oxo-2-phenylbicyclo[3.3.0]oct-6-ene | 1169969-21-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,5S)-1-aza-6-benzhydryl-7-ethoxycarbonyl-3-oxa-8-oxo-2-phenylbicyclo[3.3.0]oct-6-ene
• 英文别名: ethyl (3R,7aS)-7-benzhydryl-5-oxo-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-6-carboxylate
• CAS: 1169969-21-4
• 化学式: C₂₈H₂₅NO₄
• 分子量: 439.511
• InChiKey: IEEWQHGJWIETPG-AJTFRIOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene 、 二苯基重氮甲烷 以 丙酮 为溶剂， 以29%的产率得到(2R,5S,6S,7R)-1-aza-9,9-diphenyl-7-ethoxycarbonyl-3-oxa-8-oxo-2-phenyl-tricyclo [4.1.0^1,5.0^6,7]nonane
  参考文献：
  名称：

  A novel class of azatricyclononanes: pentasubstituted cyclopropanes from an uncatalysed reaction

  摘要：

  The direct and versatile stereoselective synthesis of a novel class of cyclopropyl derivatives of pyroglutamic acid is reported, using substituted diaryldiazo compounds. The course of the reaction has been investigated, and yields of substituted fluorenylcyclopropanes are greater than those of diphenylmethyl-cyclopropane analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.037

文献信息

• Uncatalysed diaryldiazo cyclopropanations on bicyclic lactams: access to annulated prolines
  作者：Lawrence Harris、Martin Gilpin、Amber L. Thompson、Andrew R. Cowley、Mark G. Moloney

  DOI：10.1039/c5ob00648a

  日期：——

  cycloaddition of substituted diaryldiazo compounds onto bicyclic unsaturated lactams derived from pyroglutamic acid efficiently leads to highly functionalised azatricyclononanes. The products are readily elaborated to deprotected pyroglutamate derivatives, providing rapid access to conformationally constrained amino acids and their analogues. Preliminary assessment of antibacterial activity against

  取代的二芳基重氮化合物在衍生自焦谷氨酸的双环不饱和内酰胺上的未催化环加成有效地导致高度官能化的氮杂三环壬烷。该产品易于修饰成脱保护的焦谷氨酸衍生物，可快速获得构象受限的氨基酸及其类似物。对一种革兰氏阳性和一种革兰氏阴性生物的抗菌活性的初步评估表明，在某些情况下，其疗效很高。
• A novel class of azatricyclononanes: pentasubstituted cyclopropanes from an uncatalysed reaction
  作者：Lawrence Harris、Martin Gilpin、Amber L. Thompson、Andrew R. Cowley、Mark G. Moloney

  DOI：10.1016/j.tetasy.2009.02.037

  日期：2009.5

  The direct and versatile stereoselective synthesis of a novel class of cyclopropyl derivatives of pyroglutamic acid is reported, using substituted diaryldiazo compounds. The course of the reaction has been investigated, and yields of substituted fluorenylcyclopropanes are greater than those of diphenylmethyl-cyclopropane analogues. (C) 2009 Elsevier Ltd. All rights reserved.